Sulfuric Acid → HCID 178483043, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with H2SO4 (6 mg, 0.005 mmol) and DMA (3 mL) and was degassed with N2 for 3 minutes. Pd(OAc)2 (13.5 mg, 0.005 mmol) and dppf (33.4 mg, 0.005 mmol) were added. The vial was sealed and heated at 80° C. for 30 minutes and then was cooled to room temperature. 1 mL of this solution was added to a second vial containing 5-chloro-3-{6-chloro-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-4-yl}-N,N-dimethylpyridin-2-amine (racemic, 81 mg, 0.14 mmol), Zn(CN)2 (7.8 mg, 0.06 mmol) and Zn (1.0 mg, 0.014 mmol) under an atmosphere of N2. The reaction was sealed and heated at 95° C. for 18 hours. Water (5 mL) was added, and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified on a silica gel column (0 to 50% EtOAc/hexanes) to afford 4-[5-chloro-2-(dimethylamino)pyridin-3-yl]-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (racemic). MS ES calc'd. for C29H38ClN7O [M+H]+ 534. found 534.

Provenance & Evidence